(E)-Anethol is a useful organic compound for whose fragrance is widely used in the fragrance industry for perfumes, scented candles, and numerous related products. It is also widely used in the production of alcoholic beverages such as raki, uzo, pernod, anisette, ricard, and granier where an aromatic fragrance is a part of the beverage's character. In certain countries, (E)-Anethol is used in the food and pharmaceutical industries and recently been investigated as an insect repellant as well.
Naturally occurring sources of Anethol isomers are found in the varieties of the anise, camphor, and fennel plants. (E)-Anethol is derived from these plants by a process of crushing and water distillation. The resulting amount of (E)-Anethol obtained from this process is quite low—with a 3.5% (E)-Anethol yield considered to be very good. The demand for the compound, coupled with the inefficient process used to obtain it, has caused others to try and produce a synthetic version of (E)-Anethol. Until now, those efforts have been unsuccessful. In an aspect, the disclosure provides for a novel, non-obvious and useful method for synthetically producing beta-methyl styrene compounds. In another aspect, the disclosure provides for a novel, non-obvious and useful method for synthetically producing (E)-Anethol and related compounds.
Similarly, potassium organotrifluoroborates have been shown to be an indispensable class of transformative organic reagents for wide range of cross-coupling reactions. The possible combinations of electrophiles and nucleophiles in cross-coupling reactions of allylic metals with aryl, alkenyl, and allyl electrophiles, or their reversed combination, are important due to the frequent occurrence of these fragments in natural products. In light of their low toxicity and operational simplicity, attempts have been made to use potassium allyltrifluoroborates as allylating agents. However, until now success in such efforts has been largely unknown. In another embodiment of the disclosure (E)-Anethol is synthesized from a palladium catalyst system utilizing microwave-enhanced coupling of potassium allyltrifluoroborates and aryl halides.
Transition metal catalyzed cross-coupling reaction method is extensively applied in modern chemistry for carbon-carbon bond formation reaction. Following the recent application of potassium organotrifluoroborates in organic transformations, further advances of this field especially with microwave irradiation in water have recently been made. The instant description focuses on the development of a new catalyst system for allylation reactions that involve potassium allyltrifluoroborates, organic halides as electrophiles, water as a solvent, and microwave activation.